Vibralactone Biogenesis-Associated Analogues from Submerged Cultures of the Fungus Boreostereum vibrans

Summary

This research identified six new chemical compounds produced by a fungus called Boreostereum vibrans. These compounds are related to vibralactone, which is known to inhibit fat-digesting enzymes. The study helps us better understand how fungi make these complex molecules naturally. Impacts on everyday life: • Advances our understanding of how fungi produce potentially useful compounds • Could lead to development of new drugs or enzyme inhibitors • Demonstrates new ways to study and modify natural compounds • May contribute to development of weight management treatments through lipase inhibition • Provides insights into sustainable ways to produce complex molecules

Background

The fungus Boreostereum vibrans produces vibralactone, a lipase inhibitor with an unusual β-lactone group. Previous research has identified numerous bioactive vibralactone congeners and biosynthetic-associated compounds through scale-up fermentation and culture medium modifications. The biosynthesis pathway and divergent biosynthetic routes for structurally distinct vibralactone-associated compounds have been elucidated, with 3-prenyl-4-hydroxybenzylalcohol identified as a shared biosynthetic precursor.

Objective

This study aimed to investigate trace compounds from scale-up submerged cultures of B. vibrans to identify new vibralactone biogenesis-associated analogues and expand understanding of their structural diversity and biosynthetic pathways.

Results

Six new vibralactone biogenesis-associated analogues were isolated and characterized: vibralactamide A (1), vibralactone T (2), 13-O-lactyl vibralactone (3), 10-O-acetyl vibralactone G (4), and (11R,12R)- and (11S,12R)-vibradiol (5, 6). The absolute configuration of vibralactone B was revised through single crystal X-ray diffraction analysis.

Conclusion

The study identified six previously undescribed compounds that are biosynthetically related to vibralactone. Vibralactamide A represents a novel nitrogen-containing vibralactone derivative with a different nitrogen atom-introducing pathway compared to vibralactoximes A-P. This work provides further evidence for divergent vibralactone biosynthesis pathways and expands the structural diversity of vibralactone-related compounds.
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